


Your Brother's Best Friend

by mrs_squirrel_chester



Category: Supernatural
Genre: AU, Alternate Universe, Explicit Language, Explicit Sexual Content, F/M, Gen, Oral Sex, Underage Drinking
Language: English
Status: Completed
Published: 2017-02-04
Updated: 2017-02-04
Packaged: 2018-09-21 20:59:08
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,967
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9566150
Author URL: https://archiveofourown.org/users/mrs_squirrel_chester/pseuds/mrs_squirrel_chester
Summary: You’ve had a crush on your brother’s best friend for years. One night, while playing poker with the Winchester of your choice, you decide to up the ante.





	

You weren’t supposed to feel like this, he was **your brother’s best friend**  for fuck sake. He was also 6 years older than you. Not that it made a bit of fucking difference to your raging hormones. Nope. You wanted to climb him like a monkey’d climb a tree and swing from his branches. Every glorious inch of them.

Shaking your head at the onslaught of sexual imagery your mind decided to play, you forced yourself to focus on the task at hand. Beating a certain Winchester at a game of poker.

The beer was ice cold and exactly what your parched throat craved. Scratch that. It was exactly what your parched throat was going to get since what it actually craved was currently between two thick thighs.

He chuckled low in his throat, lips pulling into a half-smirk. “You alright there, young lady?”

You hated it when he called you that. Way to remind you of the age difference. “Right as rain,” you answered, smiling tightly before laying two cards face-down on the table. “Two please.”

Ches almost looked impressed as he flicked two cards across the table. “You sure?”

“I ever bluff you before?” You looked at your cards and forced yourself to not react in any way that might give away how fucking awesome of a hand you were holding.

“Good point,” he muttered as he set down three of his own cards. He was deep in thought, brows pulled tight, bottom lip trapped between almost too-white teeth, blunt nails flicking the edges of the newest cards. And that’s when you knew you had him beat. Ches always bragged that he never developed a tell, but you’d been around him almost your entire life. Fucker had a measly pair. _Maybe_  trips.

He didn’t have many chips left so you grew bold, but not quite bold enough. Another long pull of the beer you were too young to drink gave you just enough extra courage to silence the negative voices screeching through your mind. “What d’ya say we up the ante?”

Dark eyes flicked up and it damn near took your breath away. “How much you talkin’?”

“Winner gets whatever they want,” you said, hoping he couldn’t hear the tightness in your voice. It’s not that you were a virgin. Far from it. But the man across the table had always been the forbidden fruit. And not just because he was 6 years your senior, but he was your brother’s best friend. And to top it off, he thought of you like a little sister. That was enough to make you want to quit the game and run up to your room.

Confusion flashed in his eyes. “Whatever they want?”

Another drink of beer and the bottle was empty. You decided that getting up to grab another was a good excuse to do something you’d only dreamed about. His eyes stayed on you as you stood, dumped the bottle into the recycling, and grabbed two bottles from the fridge. And they stayed on you until you stood behind him and leaned over.

With your breasts between his shoulder blades, you draped your arm over his shoulder and set the beer in front of him. Your lips were a breadth away from his ear as you whispered. “ _Whatever_  they want. And I’m not talking ‘bout money, Winchester.”

The breath caught in his throat and you could swear he failed to suppress a moan. Long fingers gripped the playing cards to the point of bowing them permanently and those perfect white teeth began to grind, his jaw clenching in a way that was oddly sexy. “Y/N, what are you playin’ at?”

Well, you’d gotten this far without him laughing in your face. Why not push it a little further?

You brushed your lips against the fleshy lobe and then nipped at it. “Who said I’m playin’?” you asked coquettishly, strutting around the table under his heavy gaze.

Ches shifted in his seat, swallowing heavily as you took your place across the table. He cleared his throat a couple times before asking, “What does all consist of?”

Shrugging, you took another long pull of beer, picking up your cards once you were satisfied, smacking your lips loudly. “Whatever the winner decides.”

A thick brow arched high on his forehead. “Anything?” he asked, voice raspy.

“Anything,” you replied before pulling your bottom lip between your teeth.

A wicked smirk played with his lips before he looked at his cards. “How many you need this time?”

“I’m good.”

You swore you heard him mutter something under his breath, but before you could ask him to repeat himself, he discarded and drew three cards.

Dark eyes scanned over the 5 cards, glittering excitedly in the shitty fluorescent lighting, and just when you were going to egg him on, the back door opened and in strolled your obnoxious brother.

“Hey, Y/N. You’re up past your bedtime, ain’t ya?” He laughed loudly, clapping his best friend on the shoulder as he rounded the table.

You rolled your eyes. “Fuck off.”

“Play nice, kid. You wound me,” your brother joked.

“Cut it out, man,” your opponent stated simply, his tone serious.

Your brother swatted his friend on the shoulder. “Words hurt, dude. And contrary to popular belief, I have feelings. I’ve been told they’re inappropriate and wrong, but they still count!”

You quickly drained your beer and slapped the cards down so hard your fingers stung. You were up from your seat and out of the room faster than both men could ask where you were going.

It was when you were halfway up the stairs you heard your brother’s teasing, “Dude, she kicked your _ass_!”

* * *

You were fresh out of the shower, wearing nothing but a tank that just barely covered your ass when there was a knock on the door. “Go away, fucker,” you called out, convinced it was your pain-in-the-ass brother.

It wasn’t his voice you heard. “It’s me. Can I come in?”

You whirled around, flinging small droplets of water off the ends of your hair as it moved. “Sure,” was your breathy reply. There was no way he heard that, right?

The knob turned slowly. Shit, he heard you. All the courage from before disappeared the moment your brother got home. Now there were butterflies in your stomach and doubt tip-toeing around your mind.

He poked his head in, eyes scanning the dimly lit room until he found you standing next to your bed. “Hey,” he muttered as he entered and closed the door slowly, knowing that if he closed it too fast, its hinges would shriek.

The butterflies that inhabited your stomach threatened to climb up your throat and you struggled to speak normally. “Thought you would’a gone home.”

One of his broad shoulders bobbed up and down and he took one step closer. “You never said what you wanted.”

“What I wanted?” you repeated, suddenly very aware of the dwindling amount of personal space you possessed with every step he took.

“For winning,” Ches breathed. He continued to cross your room, one long-legged stride at a time.

You didn’t… couldn’t answer until he was standing directly in front of you. Even then, it was the most difficult thing you’d ever said. “I want you.”

Hot breath fanned over your face when he spoke. “Finally.”

His kiss was bruising and fierce, stealing your breath and swallowing your moans with every caress of his tongue. You pushed up to your toes and molded your body to his. His hands were heavy on the small of your back and bare ass, urging you closer. His calloused hands scraped your skin like sandpaper as he squeezed one cheek, then the other, blunt nails pushing dark pink half-moons into your flushing skin.

The room was too hot and he was wearing entirely too many clothes for your liking. Grabbing the front of his plaid over shirt, you tugged on the cotton-blend, and you were instantly rewarded with the soft _ting ting_  of plastic buttons bouncing on the floor. The remainder of his clothes seemed to disappear, leaving him gloriously naked in the moonlight.

Ches didn’t give you time to worship his body like you wanted. Rather, he removed the thin tank, tossed it over his shoulder, and unceremoniously tossed you on the bed. You giggled as you bounced on your ass, sweeping the damp hair off your face.

With one long-fingered hand wrapped around his cock, he glared at you, his gaze dark and intimidating. “You’re gonna have to be quiet. You think you can do that for me?”

Curse this shitty apartment and its thin walls. You swallowed thickly, failing to clear the arousal from your voice. “I’ll do anything you want as long as you fuck me.”

It was as if those were the magic words. As you moved into a more accommodating position, he knelt on the edge of your bed and began crawling up, dropping wet kisses and scraping his teeth on your more sensitive skin.

With a low growl, he pressed his nose to your inner thigh and pulled in a deep breath. “Fuck, sweetheart. You smell good enough to eat,” he praised.

His words sent a thrill through you, landing deep in your belly and making your pussy clench. Shit, you’d never been this horny before. You grabbed your breasts roughly and expertly twisted your pert nipples. With a breathy moan, your back arched, pushing your ass into the mattress, and you drew your knees up, opening yourself to him.

Ches hissed in appreciation and dropped a kiss right above your clit. You bit back a moan and rolled your hips in an effort to urge him to continue. His chuckle was brief, sending small vibrations through your cunt before he licked a broad stripe from stern to stem, ending with a flick of his tongue to your clit. You would have begged him to keep going, but the breath was ripped from your lungs when one, then two thick fingers pushed into you, curling at the last moment.

A throaty groan fell from your mouth. This time, you were able to tell him exactly what you wanted. “Please don’t stop.”

Staring up at you between the valley of your breasts, he winked before wrapping his lips around your clit. He nipped at the aching bundle before laving it with his tongue. His fingers were dragging in and out, slowly at first, scissoring his fingers so you could take a third finger.

You tried lifting your ass off the bed to get him closer, deeper, but his other hand spread over your belly, holding you down. Your clit was overstimulated and the way he was fucking you with his hand -three fingers, three knuckles deep- was quickly driving you to the edge. Stars were littering your vision and your entire body felt like it was thrumming, like there was electricity dancing along your skin, warm and tingly, sparking as it searched for someone to shock.

The man between your legs replaced his mouth with his thumb, the blunt nail digging almost painfully into your clit as it worked furiously around it. You were gasping and writhing on the bed. “So close, so close,” you repeated over and over.

“Let go, baby. I got you,” Ches promised. The muscles in your stomach pulsed against his palm when his middle finger curled, massaging the one spot that would make you break. His reward was a slap of your hand over your mouth, followed quickly by the wet _squelch_ of your pussy as your cum began to leak out, soaking the blankets.

The strokes of his fingers continued, although they were slowing down from their previous pace. His head was bowed and he was kissing your stomach, whispering praises against your sweat-slicked skin. He removed his fingers and spread your cum all over his cock, hissing at a sting of sensitivity shot through him.

He cursed and looked at you through his lashes. “I’ve wanted this for so long, Y/N. I can’t tell you how many times I’ve dreamed about it.”

You were panting, watching hungrily as he stroked himself. “It’s you I picture when I touch myself. It’s your name I cry out when I cum. It’s always been you”

Another curse fell from Ches’ sinfully perfect lips before they were on yours, dominating, taking possession of your mouth. The wide head of his cock was sliding between your slick folds and then, he was pushing into you, slowly, until he bottomed out, his hips settling against yours. You relished in the sting, the burn of being stretched around his substantial girth, and sighed against his lips.

“Perfect. Just like I always imagined.” You raised your legs and spread them as wide as you could, the two of you grunting in approval when he sank deeper yet.

His lips curled in a snarl as he fought to control himself. Every muscle was taut, straining to remain still, to give you time to adjust. With his eyes clamped shut, a hand caressed your hip before sliding under your back and up to your shoulder, squeezing the muscle hard enough that the both of you knew you’d be wearing his mark for days to come.

You drug your nails through his hair and pulsed around his cock. His eyes flew open and he stared at you with lust-blown pupils. Ches rolled his body, barely able to keep from moaning your name loudly. Smirking, you held a finger to your lips briefly before kissing him, giving his cock another squeeze.

Any self-control he might have still possessed shattered and, with a feral moan, he pulled almost completely out, driving himself home that was echoed with a thick, wet slap of his balls on your ass. Long fingers dug deep into your shoulder as he used your own body for leverage, his thrusts growing stronger and more powerful. If you were going to wear his mark, he’d be wearing yours. You clawed at his slick back -leaving a trail of angry red welts- and grabbed his ass, pulling him into you harder and faster. You were both moaning and grunting with each thrust of his hips, your own snapping up, meeting him halfway.

The all too familiar pressure of your orgasm started to grow, rising up and flowing out like lava, searing everything it touched. “Fuuuuuck, Winchester,” you ground out.

His shoulders were bowing, stretching his tanned skin taut, the thick muscles below flexing and jumping with every flex and thrust. His knees spread wide, pushing his thighs into your own, spreading you open like a goddamn buffet. He was pounding into you relentlessly, the bed springs squeaking loudly in protest.

“I need you to cum, Y/N. Please,” he begged, his voice completely shattered.

It was the please that did it. You came with a strangled cry of his name, pulsing around him, shuddering under him. His sweat-dampened forehead was on your pillow, face buried in your neck, lips and teeth on your flesh as he came, your name echoing in your ear as he came. His whole body was shaking as his balls drew up and his cock swelled and pulsed. The pair of you grunted as waves of pleasure continued to course through you, squeezing and pulsing sensitive flesh until it hurt, but in a way that you didn’t want to stop.

Only after he started to go soft, did he move. Rolling to the side, he kept his arm around you and pulled you with him, continuing to kiss you languidly long after his cock stopped twitching. You scraped your nails along his scalp as his own fingers carded through your hair.

His eyes were sparkling when you pulled back. “So… that happened,” you rasped.

“Yeah,” he agreed, nudging your nose with his. “I’m glad it did, though.”

You saw the hesitation in his eyes, that it would break him if this was only a one-time thing to you. You kissed him sweetly. “Me, too.”

* * *

It was early afternoon, and the two of you were in the kitchen. Ches sat at the table, drinking a steaming cup of coffee and scanning the paper while you doctored up your coffee to an acceptable mixture of bitter and sweet. You could literally feel the weight of his gaze on your ass and you’d be lying if you said it didn’t make your stomach flip lazily.

Turning around revealed your brother standing in the doorway. His eyes were wide and dragging over you. The red and purple bruises acquired last night and this morning were in plain sight. There was no amount of makeup that would cover them. Not that you wanted to. You were proud of them.

“What the hell happened?” he demanded, clearly pissed that someone had done something to his kid sister.

Ches barely covered a laugh with a cough and all you did was shoot him a wink while sipping your coffee. Despite not being the brightest crayon in the box, your brother didn’t miss the exchange. His dark eyes narrowed as they settled heavily on the man he had known his entire life.

“She’s my sister, Winchester. What the fuck?”

Standing tall, Ches walked over to you and dropped a kiss to the top of your head. “If he kills me, promise me you won’t mourn me too long,” he joked, voice thick with laughter. And then he sprinted out the back door, his bare feet slapping against the dew-damp concrete.

Your brother tore off after him, shouting promises of kicking his ass and all you could do was roll your eyes as you sat down where he had been sitting.

A brightly colored ad caught your attention. “Oooo, mattresses are on sale.”


End file.
